King Frederic announces the five hundredth Good Will Gopher Grab, a festival set around a gopher running wild around an arena with people trying to catch it, the one who succeeds wins. As it is Rapunzel's first festival, she redesigned the "Gopher Grab Seal of Good Will", which acts as the price of the competition. As the king lifts the covering everyone cheers for Rapunzel except for one man booing her. The princess' inexperience leads to her thinking that this is also a cheer.
Later as she walks through town with Eugene he comments on how the people of the kingdom like her. Rapunzel is proud and, not knowing what "Boo" means, happy about that. Eugene tells her to forget it but Rapunzel still doesn't notice her mistake. It's up to Cassandra and Eugene to tell her the meaning of the cheer as she calls it. Naturally, she is shocked when Cassandra tells her what the person really meant: He hates her. This causes Rapunzel to wonder why the man does not like her and what his reason was. While Eugene and Cassandra who is in charge of taking care the gopher for the tournament as it represents tradition try to tell her that not everyone has to like everyone else, she means to ignore at first it but failed. As she tries to calm herself down at a café she finally sees the person responsible for her state of mind: a nice, little old man. As he rides by in a carriage he booes her again shocking the princess even more and making her determined to win him, her naysayer, over.
Back at the castle she paints a picture of this man as Eugene bursts in and identifies the man as Monty. Rapunzel asks why he knows him and unfortunately Eugene's answer is not quite what she expected as he tells her that Monty is well known for being a nice, sweet guy not for being rude. Eugene is equally shocked as he finds out Monty booed Rapunzel because of Monty's reputation of being the nicest man in town. He tries to fix his mistake by claiming it is not Monty but fails as Stan the Guard comes in, recognizing him as Uncle Monty who is loved by everyone. He draws Rapunzel a map to his shop, but spelling it "Sweat shop" instead of "Sweet shop". Rapunzel leaves against Eugene's advice believing it's just a simple misunderstanding between her and Monty.
After that Eugene goes to Cassandra who is still busy with preparing the gopher for the festival. He doesn't understand why Rapunzel is so determined to win over her naysayer. Cassandra bluntly leaves him alone with the gopher to get something and after she leaves he starts eating the bim-berries which were supposed to be eaten by the gopher. Upon arriving in town she is at first surprised as she wonders why someone would like a Sweat shop owner as she realizes it is a sweet shop he owns. She steps in and sees Monty as he gives chocolate to the children, noticing the gopher grab seals on the wall. Eventually she approaches him and tries to be friendly to him but Monty refuses to be nice to her even purposely giving her candy which was lying on the floor. As Rapunzel tries to clear the situation he accuses her of trying to throw him into the dungeon for booing her at the ceremony and makes her go out brokenhearted and more determined than ever to win him over.
She starts by making a green scarf for him but he throws it back in her face, apparently because he doesn't like the color. Her next project is making a chocolate sculpture of Monty's head but he complains about it being hollow and throws her and the sculpture out again. Rapunzel now tries decorating his shop sign by painting it. To her shock that still doesn't satisfy Monty as he yells at her it was from his great-grandfather. As nothing she does seems to have any effect she joins Eugene as he sits a tent, still eating berries. Rapunzel falls depressingly on a couch. Cassandra tells her to give up but she refuses to do so and decides to disguise herself to make friends with him.
Rapunzel, now with a brown wig, glasses and a long orange cloak hiding her hair, visits Monty in his shop. She trips over her statue but Monty catches her before she can hit the ground. He tells her he intended to use the sculpture she made as a door stopper. Now Monty asks for her name, naturally she doesn't want him to find out who she really is and says her name is Miss Misty. After she orders some jelly beans, not the green ones, he starts to like her and gets her the jelly beans from his personal storage where he already picked out his least favorite ones. Back at the tent Cassandra notices that the bim-berries are gone and immediately blames Eugene who denies it at first but has to give in as there is still berry juice on his teeth. Cassandra gets mad and harshly orders him to get some new bim-berries as she needs the gopher to run at the festival.
Meanwhile, Rapunzel, still in disguise, enjoys having Monty tell some stories about how his ancestors won the gopher grab. His wish is to win it too but every time it slipped through his fingers. To cheer himself and his new friend up, he leads her to a statue of Rapunzel and throws tomatoes at it and after her request he tells her he loathes the princess but before he can tell her the reason they are interrupted by the bells ringing indicating that the festival is starting soon. Monty runs to the location where the event will take place with "Misty" following him. She suggests to take part in the tournament together which Monty gladly accepts.
In the meantime Eugene got dim-berries for the gopher and Cassandra is too busy to notice that the berries Eugene brought are the wrong ones. She feeds them to Gregorial the gopher but as the animal eats really slowly Eugene buys her time by giving a speech in front of the competitors. Cassandra brings in the gopher locked in a toy castle at just the right moment but as she opens the door the gopher at first doesn't come out. Unfortunately, after a few seconds the now crazy gopher storms out faster than ever because of the dim-berries it was given by mistake. Monty catches it but it slips through once again. Cassandra finally realizes Eugene brought the wrong berries and is angry with him for that as it causes hyperactivity in rodents.
Nobody succeeds in catching the gopher as it's simply to fast and knocks everyone over. Since it was fed the wrong berries it gets so hyperactive that it digs a tunnel beneath the borders of the arena. Monty is determined to win and follows it into the woods with "Misty" behind him. They find the animal on a rock in a river. Monty wants to get to it by jumping over the rocks while Rapunzel suggests catching him on the other side by walking over a bridge. The proud man doesn't listen, trips while trying to get the gopher and falls into the river which leads to a huge waterfall. Rapunzel tries to save him by getting him from the bridge mentioned before but as she stands on it, it starts breaking. As she gets Monty's hand the bridge gets even more unstable and is close to breaking leading her to lose her partner's hand. The man falls down the waterfall but is saved by Rapunzel who decided to let go of the disguise and used her hair to swing down the waterfall and save Monty.
Finally Rapunzel gets to know why he booed her, the reason being that she redesigned the traditional good will seal. He tells her how important tradition is to him and how she changed it since she came back. Still he admits she did inspire him to complete his dream of catching the gopher which is found in his pocket. After that they decide they'll never be friends as Monty still doesn't like her tricking him and Rapunzel finally accepts not everyone has to like her and she realizes she doesn't like him either. In the end they shake hands, agreeing on not being friends, Monty wins the seal, as he gets it, Rapunzel booes him, and hangs it in his shop next to those of his forefathers and smiles at it.
- Mandy Moore as Rapunzel
- Zachary Levi as Flynn Rider
- Clancy Brown as King Frederic
- Eden Espinosa as Cassandra
- Richard Kind as Monty
- Diedrich Bader as Stan
- Monty's design was inspired by a mix of Captain Kangaroo and Eric Goldberg.